N,N,N',N',N'',N''-Hexamethylmethanetriamine → 5-phenoxy-1H-indole

HRID 1371890

반응식

HRID 1371890 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:6][C:5]=1[CH3:17])([O-])=O.[CH3:18]N(C(N(C)C)N(C)C)C.[H][H]>C1(C)C=CC=CC=1.CCOC(C)=O.[Pd]>[O:10]([C:7]1[CH:6]=[C:5]2[C:4](=[CH:9][CH:8]=1)[NH:1][CH:18]=[CH:17]2)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

참가 물질

7

반응물 3

HCID 79831N,N,N',N',N'',N''-HexamethylmethanetriamineHCID 27284182-Nitro-5-phenoxytolueneHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 112412535-phenoxy-1H-indole

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

Combine 2-nitro-5-phenoxytoluene (1.15 g, 5.0 mmol) and tris(dimethylamino)methane (0.87 g, 6.0 mmol) in 10 mL dry toluene and heat to reflux under nitrogen. After 2 hours, cool the reaction mixture to room temperature and evaporate the toluene under reduced pressure to form a residue. Dissolve the residue in 15 mL EtOAc, mix with Pd/C (10%, 100 mg), stir at room temperature under 1 atmosphere of hydrogen for 1.5 days. Filter off catalyst and concentrate the filtrate. Chromatograph on silica gel eluting with hexanes/EtOAc give the title compound as a solid: 1H NMR (300 MHz, CDCl3) 6.49–6.50 (m, 1H), 6.93–7.03 (m, 4H), 7.22–7.27 (m, 5H), 8.15 (br, 1H).

후처리

  1. temperatureto reflux under nitrogen
  2. customevaporate the toluene under reduced pressure
  3. customto form a residue
  4. filtrationFilter off catalyst
  5. concentrationconcentrate the filtrate

출처 및 근거

ORD 기록
ord-106d28dc5c944e1bad71daa18b56160f
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07157488B2

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